Chappelle is perhaps best known for his sketch comedy program “Chappelle’s Show” on Comedy Central. The broadcast ran from 2003-2005 and parodied such topics as racial stereotypes, politics, and pop culture. TV Guide put “Chappelle’s Show” #31 on their list of "TV's Top 100 Shows,” and it placed #26 on Entertainment Weekly's
"New TV Classics."
However, long before all of this I encountered Chappelle in Downtown Detroit. Here’s that story.
It was April 2001, and I had a late dinner with a group of friends on a Friday night in Greektown. Following our meal, we walked past the Atheneum Hotel around 11 o’ clock. There, I spotted Chapelle, alone and smoking a cigarette. He wore jeans and a jean jacket, donned a bucket hat, and carried a backpack.
“Are you Dave Chappelle?” I asked.
“Yep! Sure am!” he answered enthusiastically.
I stopped to chat for a bit. I asked him what he was doing, and he told me he had just performed a stand-up show at the nearby State Theater (now The Fillmore Detroit). I told him I enjoyed his humor and he expressed sincere gratitude. He said something like, “Thank you! Thank you! Appreciate that!”
Meanwhile, my amigos remained off to the side. They had no idea who he was and neither did any other pedestrians. “This guy is a comedian!” I tried to explain. “He’s funny! He’s on TV and in movies!” This was two years before “Chappelle’s Show” debuted, so the world had yet to hear the phrase “I'm Rick James, b***h!“ At this point, he was perhaps best known for his appearances on “Late Night with Conan O’Brien,” and supporting roles in movies, including “The Nutty Professor,” “Con Air,” and “Robin Hood: Men in Tights.”
Chappell as Rick James and in "Robin Hood."
Our encounter ended when Chappelle asked us – I'm not making this up – if we could take him to a party. I was open to the idea, and I asked the group if they knew of anything. They, however, found his request odd and suggested we leave. (I thought it was a nice gesture! He took us for good people and wanted to hang out!) So, we left him as we had found him, milling about and enjoying a smoke.
I still wonder, more than 16 years later, what would have happened if we had taken him to a wingding. What stories might have come out of it? It remains a great unknown.